Inter-oxa-9-deoxy-PGD1 compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particlarly and especially as blood platelet aggregation inhibitors.

The present application is a divisional application of Ser. No. 614,244,filed Sept. 17, 1975, now pending. United States Ser. No. 809,248, filedJune 23, 1977, and also a divisional application of Ser. No. 614,244,has now issued as U.S. Pat. No. 4,099,014.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,099,014.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein m is1 to 5, inclusive; WHEREIN M₁ is ##STR3## wherein R₅ and R₆ are hydrogenor methyl, with the proviso that one of R₅ and R₆ is methyl only whenthe other is hydrogen;Wherein L₁ is ##STR4## wherein R₃ and R₄ arehydrogen, methyl, or fluoro, being the same or different, with theproviso that one of R₃ and R₄ is fluoro only when the other is hydrogenor fluoro; Wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms,inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, two,or three chloro or alkyl of one to 3 carbon atoms, inclusive, or apharmacologically acceptable cation; and Wherein Z₈ is(1) --CH₂ --O--CH₂--(CH₂)_(g) --CH₂, (2) --(ch₂)₂ --o--(ch₂)_(g) --CH₂ --, or (3) --(CH₂)₃--O--(CH₂)_(g) --,Wherein g is 1, 2, or
 3. 2. A compound according toclaim 1, wherein M₁ is ##STR5##
 3. A compound according to claim 1,wherein M₁ is ##STR6##
 4. A compound according to claim 3, wherein m is3.
 5. A compound according to claim 4, wherein Z₈ is

    --CH.sub.2 --O--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --.


6. A compound according to claim 5, wherein g is
 3. 7. A compoundaccording to claim 5, wherein g is
 1. 8. A compound according to claim7, wherein R₅ and R₆ are both hydrogen.
 9. A compound according to claim1, wherein R₃ and R₄ are both hydrogen.
 10. 5-Oxa-9-deoxy-PGD₁, acompound according to claim
 9. 11. A compound according to claim 8,wherein R₃ and R₄ are both fluoro. 12.16,16-Difluoro-5-oxa-9-deoxy-PGD₁, a compound according to claim
 8. 13.A compound according to claim 4, wherein Z₈ is

    --(CH.sub.2).sub.3 --O--(CH.sub.2).sub.g --.


14. A compound according to claim 13, wherein g is
 3. 15. A compoundaccording to claim 14, wherein R₅ and R₆ are both hydrogen.
 16. Acompound according to claim 15, wherein R₃ and R₄ are both hydrogen. 17.2a,2b-Dihomo-3-oxa-9-deoxy-PGD₁, a compound according to claim
 16. 18. Acompound according to claim 15, wherein R₃ and R₄ are both fluoro. 19.2a,2b-Dihomo-16,16-difluoro-3-oxa-9-deoxy-PGD₁, a compound according toclaim
 18. 20. A compound according to claim 13, wherein g is
 1. 21. Acompound according to claim 20, wherein R₅ and R₆ are both hydrogen. 22.A compound according to claim 21, wherein R₃ and R₄ are both hydrogen.23. 3-Oxa-9-deoxy-PGD₁, a compound according to claim
 22. 24. A compundaccording to claim 21, wherein R₃ and R₄ are both fluoro. 25.16,16-Difluoro-3-oxa-9-deoxy-PGD₁, a compound according to claim 24.